Abstract
The pKa values for the 5- and 6-aminoindoles were determined from potentiometric titration curves and from 13C NMR data on the total change of the chemical shifts of the carbon atom signals on protonation of the amino group. The pKa values obtained (5.99 and 5.53) were higher than those of aniline (3.92) or Β-naphthylamine (3.39).
Similar content being viewed by others
Literature Cited
I. A. Petrunin, L. Kh. Vinograd, N. M. Przhiyalgovskaya and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 8, 1050 (1987).
J. Herley-Mason and A. H. Jackson, J. Chem. Soc., No. 3, 1158 (1954).
R. K. Brown and N. A. Nelson, J. Am. Chem., 76, 5149 (1954).
H. E. Johnson and D. C. Grosly, J. Org. Chem., 28, 2794 (1963).
B. D. Astill and V. Boekelheide, J. Org. Chem., 30, 1538 (1955).
J. I. De Graw, Canad. J. Chem., 44, 387 (1966).
A. P. Terent'ev, M. N. Preobrazhenskaya, A. S. Bobkov, and G. M. Sorokina, Zh. Org. Khim., 29, 2504 (1959).
R. Ikan and E. Rapoport, Tetrahedron, 23, 3823 (1967).
H. F. Russell, B. J. Harris, D. B. Hood, E. G. Thompson, A. D. Watkins, and R. D. Williams, Org. Prep. Proc., 17, 391 (1985).
S. N. Krasnokutskii and L. N. Kurkovskaya, Thesis Report, 1st All-Union Conference, “Chemistry, Biology, and Pharmacology of Indole Derivatives,” Tbilisi, (1986), p. 87.
B. Gutbezahl and E. Grunwald, J. Am. Chem. Soc., 75, 559 (1953).
R. F. M. Sureau, Bull. Soc. Chim. France, No. 4, 622 (1956).
G. Levy and G. Nelson, in: 13C Nuclear Magnetic Resonance, Wiley, New York (1980).
Author information
Authors and Affiliations
Additional information
For Communication 130, see [1].
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, 766–769, June, 1988.
Rights and permissions
About this article
Cite this article
Salekh, M.A., Kurkovskaya, L.N., Krasavina, L.S. et al. Indole derivatives. 131. The basicity of 5- and 6-aminoindoles. Chem Heterocycl Compd 24, 624–627 (1988). https://doi.org/10.1007/BF00475595
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00475595